Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Base Information

• Chemical Name: Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate
• CAS No.: 177036-78-1
• Molecular Formula: C17H18O4
• Molecular Weight: 286.328
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID50442875
• Wikidata: Q72484808
• Mol file: 177036-78-1.mol

Synonyms:177036-78-1;Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate;(S)-2-HYDROXY-3-METHOXY-3,3-DIPHENYLPROPIONIC ACID METHYL ESTER;Methyl(2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate;SCHEMBL2354447;DTXSID50442875;AMY14980;FD7218;MFCD11865341;AKOS015999150;AC-26423;AC-26424;AS-73060;CS-0061795;A881481;Methyl (S)-2-Hydroxy-3-methoxy-3,3-diphenylpropionate;(S)-2-Hydroxy-3-methoxy-3,3-diphenylpropanoic acid methyl ester;Benzenepropanoic acid, alpha-hydroxy-beta-methoxy-beta-phenyl-, methyl ester, (alphaS)-

Chemical Property of Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate

Chemical Property:

• Appearance/Colour: Almost White To White Powder
• Boiling Point: 440.7±40.0 °C(Predicted)
• PKA: 12.37±0.20(Predicted)
• PSA: 55.76000
• Density: 1.176
• LogP: 2.11050
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 286.12050905
• Heavy Atom Count: 21
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

(S)-α-Hydroxy-β-methoxy-β-phenyl-benzenepropanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C(C1=CC=CC=C1)(C2=CC=CC=C2)OC)O
• Isomeric SMILES: COC(=O)[C@H](C(C1=CC=CC=C1)(C2=CC=CC=C2)OC)O
• Uses: (S)-α-Hydroxy-β-methoxy-β-phenyl-benzenepropanoic Acid Methyl Ester is an impurity in the synthesis of Ambrisentan (A575860), a nonpeptide endothelin ETA receptor antagonist. Antihypertensive. (Ambrisentan Hydroxyester Impurity)

Technology Process of Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate

There total 8 articles about Methyl (2S)-2-hydroxy-3-methoxy-3,3-diphenylpropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.11%

dimethyl sulfate (77-78-1) + (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (178306-52-0,178306-49-5) → (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester (177036-78-1)

Guidance literature:

With sodium methylate; In N,N-dimethyl-formamide; at 5 - 28 ℃; Inert atmosphere;

Reference yield: 92.6%

methyl 3-methoxy-2-oxo-3,3-diphenylpropionate (1431363-04-0) → (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester (177036-78-1)

Guidance literature:

With potassium phosphate; keto-reductase enzyme KRED-P₁-B₁₂; NADP; magnesium sulfate; In water; dimethyl sulfoxide; isopropyl alcohol; at 25 - 30 ℃; Enzymatic reaction;

Reference yield:

(S)-2-hydroxy-3-methoxy-3,3-diphenyl propionic acid (178306-51-9,178306-49-5) → (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester (177036-78-1)

Guidance literature:

Multi-step reaction with 2 steps

2: 55.8 g / sodium methoxide / dimethylformamide

With sodium methylate; In N,N-dimethyl-formamide;

DOI:10.1021/jm9910425

upstream raw materials:

dimethyl sulfate

(S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid

(S)-2-hydroxy-3-methoxy-3,3-diphenyl propionic acid

methanol

Downstream raw materials:

(S)-methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate

(S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester

ambrisentan

darusentan

Refernces

• 1、 -. "Improved Process For The Preparation Of Endothelin Receptor Antagonists". . . Retrieved 2011/11/06.
• 2、 -. "IMPROVED PROCESS FOR THE PREPARATION OF ENDOTHELIN RECEPTOR ANTAGONISTS". Page/Page column 20. . Retrieved 2010/08/05.